


Can I Measure Up?

by ninaloveshiddles



Category: SPN, Supernatural
Genre: Eavesdropping, Emotional Hurt/Comfort, F/M, Fucking, Hair-pulling, I Love You, Insecurity, Kissing, Loss, Love Confessions, Making Love, Nipple Licking, Nipple Play, Showers, Vaginal Sex
Language: English
Status: Completed
Published: 2016-01-04
Updated: 2016-01-04
Packaged: 2018-05-11 14:43:37
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,534
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5630293
Author URL: https://archiveofourown.org/users/ninaloveshiddles/pseuds/ninaloveshiddles
Summary: <blockquote class="userstuff">
              <p>The reader is in a relationship with Sam Winchester. However, she becomes sad and anxious because she's worried he's still in love with Jess. Will she ever measure up to his "true love?"</p>
            </blockquote>





	Can I Measure Up?

**Author's Note:**

  * For [Sigyn Winchester](https://archiveofourown.org/gifts?recipient=Sigyn+Winchester).



> Sorry this took so long. I've been incredibly busy and haven't written for about three months, but I"m slowly trying to get back in it. I'm sure this is far too late, but I hope you like it.

“Oh my god!” you scream out, as the muscles in your abdomen spasm. Sam’s thick cock pushes in again, stretching your tight hole to the fine line of pain and pleasure.

“Are you ok baby?” he asks in a husky voice, his arms trembling. He is holding himself over you, his long hair brushing over his beautiful hazel eyes.

“So good” you gasp, biting your lip. You want it, you need it. It’s so intimate, too deep, yet not close enough.

Sam grins, his dimples showing beautifully, even in the darkness. He slides in again, splitting you wide open. You wrap your legs around his waist, willing his body farther in.

“Kiss me” you whisper, your mouth dry from your heavy breathing. Sam practically growls as he lunges, his lips capturing yours. You moan into his mouth as he conquers and explores with his tongue. He tastes so sweet, so comforting. His lips are soft and warm, crafting to yours as if they were made for each other. You whimper softly as his pelvis picks up the pace, moving back and forth, pounding you rapidly. Your walls clench around his hard dick. It feels so good, your head is turning left to right, your hair moving wildly against the pillow. Sam just chuckles at you, finding your pleasured eye crossing adorable.

“You’re so gorgeous” he grunts, his teeth scraping against your ear. You can only moan loudly, threading your fingers into his soft brown hair, gripping tightly. You earn a deep moan from Sam’s throat, and it makes your pussy burn. His mouth finds your nipple, and he teases mercilessly with his tongue as he rocks in and out of you. His teeth tug, sending pleasure shocks through every nerve in your body. He sucks, and you tighten your thighs around him, a high whine escaping your parted lips.

“I’m getting close” he whispers, and you detect a nervousness in his voice. You lock in on each other, his eyes shining brightly, filled with wonder and uncertainty.

“It’s ok” you nod, wanting your release as well. “Make us cum together baby” you mutter. He slams into you, going deep, nailing your sweet spot. Your bodies glistening with sweat, the smell of each other intoxicating. He nails you again and you scream out with need and a fiery lust. You feel yourself building with every pound, contracting and rubbing, delicious friction sending you higher and higher. Finally, you topple over as you hear Sam scream your name, riding your orgasm out with him.

He drops on top of you, exhausted and shaken. You hold him, suffocated by his weight, but comforted. He clings to you as you both try to breathe normally. He finally rolls over, lying next to you. He takes your hand and turns to you, a guarded smile on his face.

“I’’m –uh, glad we did that.” You grin widely at him, nodding eagerly. You and Sam Winchester have been going out for about three months, but you had been hunting with him and Dean for almost a year. You began to worry that he was never going to make a move. You were his first serious girl since Jessica. He didn’t talk much about her with you, but it was obvious he loved her. He was even going to ask her to marry him. You had been concerned that he would never get over her, but maybe tonight proved that he had moved on?

He gives you a sad smile, and then his brows furrow. “What is it?” you ask, analyzing every inch of his face.

“I’ll be right back” he mutters under his breath. He grabs his jeans and throws on a shirt quickly, walking out of the motel room. When you hear the door shut, you bolt out of the bed and creep over to the door, making sure he can’t see you through the windows. You put your ear up to the door, desperate to know what was going on.

“Dean?’ you hear Sam say; he must be on his cell phone.

“Yeah we did…good, uh very good” he says awkwardly. “Well uh; it’s just, Jess you know?” Your heart flutters a bit, and your stomach gets nervous. _Jessica? Shit, he shouldn’t be thinking about a dead girlfriend at a time like this._ “I just, it hurts. You know what she means to me…” you clap a hand over your mouth and crawl backward away from the door. Hot tears begin to stream down your cheeks and you run to the bathroom. You turn on the shower and hop in, not waiting for it to get warm. You’re still naked from before, and the cold water shocks your skin, but you need to clear your head. You haven’t told him yet, but you love Sam. Hearing that he still thinks about Jess? That she means that much to him still? It’s devastating. You thought you finally found someone who could actually give you the love you deserve.

The water runs down your body, finally warming you up and your shivers begin to cease. You lean your head against the smooth wall in the shower, letting the sobs come out. _What’s so damn special about her? You’ll never be able to measure up to her. She was prettier than you. Smarter than you. Probably more charming._ You’re disturbed from your thoughts by a sudden loud knock, startling you.

“Hey, (y/n)? You want any company?” Sam calls.

“Not now” you manage, barely keeping your voice from cracking.

“What’s wrong?” he asks more forcibly, his voice etched in concern.

“Sam please, just go away” you plead, a sob caught in the back of your throat. Sam hears it and opens the door; why the fuck didn’t you lock it? You hear his bare feet against the tiles, getting closer. His silhouette visible against the shower curtain.

“Baby?” he says softly.

“Please leave me alone” you say softly, hugging yourself under the stream of the water. You see his shadow back away slightly, and you think he’s going to leave without a fight. Suddenly you hear clothes hit the floor, and his large frame tears into the shower behind you.

“What are you doing?” you demand, turning to face him. You try to ignore the water dripping deliciously down his abs, and oh Jesus. Even soft his cock is huge. You shake your head slightly and force yourself to maintain eye contact.

“I’m not leaving until you tell me what’s wrong. I’m not losing another girl I care about” he says carefully, clearly worried about you.

You sniffle, resentment still in your heart. “Another one? Like you really care about me that much. Did you even want to sleep with me?”

“What the hell are you talking about?”

“Sam, I’m never going to measure up to Jessica am I? You don’t talk about her with me, but I know how much she meant to you. And I get it” you take a deep breath, breaking eye contact, it’s too painful. “But I deserve someone who’s actually going to love me, not think about someone else more than me.”

You wait for Sam to leave, certain there is nothing he can say. “Shit, (y/n)” he whispers. He grabs you, holding you against his chiseled body, warm and slippery. Your lip trembles, surprised by the show of affection.  “How can you say that?” he asks, and you’re suddenly embarrassed by your outburst when you hear the pain in his voice.

“I heard you on the phone” you whisper against his wet skin, tears continuing to pour from your eyes. “You said ‘it hurts’, and ‘you know what she means to me.’”

“Babe-“

“And I get it. She was a college girl, I’m sure smarter and prettier than me. I mean, you wanted to marry her-“ you’re interrupted by Sam’s lips on yours, loving and earnest.

“(Y/n). Yeah I loved her, she was my first love. But babe; you’re the one I want. And it does hurt, because for the first time in my life, I don’t miss her. You helped me move on, you healed the hole that was left in my heart. It’s just a whole new experience and it scared me. And when I was talking about how much she means to me, I meant you. It hurts to care this much about someone again, because I’m scared of losing you. But believe me, you’re everything I’ve ever wanted. I love you!”

Your chest constricts and you look up into his eyes, getting lost in them. “I love you too” you whisper. He grins widely, absolutely relieved.

His lips meet yours, and his muscular arms wrap protectively around your frame.  You move your lips against his, your tongue pushing into his mouth, teasing him. You put your hand in his wet hair, grinding your body up against his.

“What do you say to round two?” he growls in your ear, his voice rough and sexy.

You just moan in his ear, unable to lose your smile. Happiness is radiating through you, and you finally feel safe, finally feel like you belong somewhere, like you’re worth it.

“Hell yes.”

 

**Author's Note:**

> Thanks for reading!


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